CH308694A - Process for the preparation of the chlorohydrate of dimethylaminoethyl ester of 4-n-butylamino-2-oxy-benzoic acid. - Google Patents
Process for the preparation of the chlorohydrate of dimethylaminoethyl ester of 4-n-butylamino-2-oxy-benzoic acid.Info
- Publication number
- CH308694A CH308694A CH308694DA CH308694A CH 308694 A CH308694 A CH 308694A CH 308694D A CH308694D A CH 308694DA CH 308694 A CH308694 A CH 308694A
- Authority
- CH
- Switzerland
- Prior art keywords
- ester
- benzoic acid
- oxy
- butylamino
- hydrochloric acid
- Prior art date
Links
- 239000005711 Benzoic acid Substances 0.000 title claims description 17
- -1 dimethylaminoethyl ester Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- YCCRFDDXAVMSLM-UHFFFAOYSA-N 4-(butylamino)benzoic acid Chemical compound CCCCNC1=CC=C(C(O)=O)C=C1 YCCRFDDXAVMSLM-UHFFFAOYSA-N 0.000 claims description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 4
- 230000001988 toxicity Effects 0.000 claims description 4
- 231100000419 toxicity Toxicity 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 241000700159 Rattus Species 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims description 2
- 230000003444 anaesthetic effect Effects 0.000 claims description 2
- 230000003385 bacteriostatic effect Effects 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229960003920 cocaine Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 238000007912 intraperitoneal administration Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 230000001549 tubercolostatic effect Effects 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung des Chlorhydrats des Dimethylaminoäthylesters der
4-n-ButyIamino-2-oxy-benzoesÏure.
Im Schweizer Patent Nr. 305885 wurde die therapeutische Bedeutung der Ester N-monoalkylierter 4-Amino-2-oxy-benzoesäure mit am Stickstoffatom alkylierten Aminoalkoholen erwÏhnt und ein Verfahren zur Herstellung des Chlorhydrats des Diäthylaminoäthylesters der 4-n-Butylamino-2-oxy-benzoesäure beansprucht.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung des Chlor liydrats des Dimethylaminoäthylesters der 4-n-Butylamino-2-oxy-benzoesäure, welches dadurch gekennzeiehnet ist, dass man den Di methylaminoäthylester der 4-Amino-2-oxyhenzoesäure mit Butyraldehyd kondensiert und das Reaktionsprodukt durch Behand lung mit Wasserstoff in Gegenwart eines Katalysators hydriert. Anschliessend wird das IIydrierungsprodukt mit Salzsäure angesäuert, wobei als Endprodukt das Chlorhydrat des gew nschten Esters erhalten wird.
Die so erhaltene neue Verbindung ist eine farblose, kristalline Substanz vom Sehmp. 156-157 C, die bei 20 C in etwa 25 Teilen Wasser los- lieh ist. Sie soll als Arzneimittel verwendet werden.
Beispiel :
22, 4 g-4-Amino-2-oxy-benzoesauredimethyl- aminoÏthylester und 1 cm3 konzentrierte Salzsaure werden in 250 em3 Isopropylalkohol ge lost. Die Losung wird in einer Druckflasche bei Raumtemperatur nach Zugabe von 1 g PtO mit Wasserstoff unter kontinuierlichem Zutropfen von 14, 4 g N-Butyraldehyd in 80 em3 Isopropylalkohol geschüttelt. Nach Beendigung der Wasserstoffaufnahme wird filtriert und die Lösung auf ein Volumen von 50 em3 eingeengt.
Nach Zugabe von äthyl- alkoholischer Salzsäure bis zum p-Wert von 4-5 kristallisiert das salzsaure Salz des 4-Di- methylaminoäthylesters der 4-n-Butylamino-2oxy-benzoesäure aus, das nach dem Umkristallisieren aus Wasser einen Schmelzpunkt von 156 C zeigt.
Dieser Ester weist bei annähernd gleicher anästhetischer Wirkung eine wesentlich geringere Giftigkeit als der Dimethylaminoäthyl- ester der 4-Butylamino-benzoesäure auf. Das Verhältnis der Toxizitäten des neuen Esters zum bekannten Ester der 4-Butylamino- benzoesäure beträgt bei der Testung an Ratten intraperitoneal und bezogen auf Cocain = 1 annähernd 0, 9 : 2, 5. Ausserdem weist der neue Ester eine bakteriostatische, insbesondere tuberkulostatische Wirkung auf.
PATENTANSPRUCH :
Verfahren zur Herstellung des Chlorhydrats des Dimethylaminoäthylesters der 4-n Butylamino-2-oxy-benzoesäure, dadureh gekennzeichnet, dass man den Dimethylamino äthylester des 4-Amino-2-oxy-benzoesäure mit
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of the hydrochloride of dimethylaminoethyl ester
4-n-Butylamino-2-oxy-benzoic acid.
In Swiss patent No. 305885 the therapeutic importance of the esters of N-monoalkylated 4-amino-2-oxy-benzoic acid with amino alcohols alkylated on the nitrogen atom was mentioned and a process for the preparation of the chlorohydrate of the diethylaminoethyl ester of 4-n-butylamino-2-oxy- benzoic acid claimed.
The subject of the present patent is a process for the preparation of the chlorine liydrate of dimethylaminoethyl ester of 4-n-butylamino-2-oxy-benzoic acid, which is characterized in that the dimethylaminoethyl ester of 4-amino-2-oxyhenzoic acid is condensed with butyraldehyde and that Reaction product is hydrogenated by treatment with hydrogen in the presence of a catalyst. The hydrogenation product is then acidified with hydrochloric acid, the end product being the chlorohydrate of the desired ester.
The new compound thus obtained is a colorless, crystalline substance from Sehmp. 156-157 C, which is loosened at 20 C in about 25 parts of water. It is intended to be used as a medicine.
Example:
22.4 g of 4-amino-2-oxy-benzoic acid dimethyl amino ethyl ester and 1 cm3 of concentrated hydrochloric acid are dissolved in 250 em3 of isopropyl alcohol. The solution is shaken in a pressure bottle at room temperature after adding 1 g of PtO with hydrogen with the continuous dropwise addition of 14.4 g of n-butyraldehyde in 80 cubic meters of isopropyl alcohol. After the uptake of hydrogen has ended, it is filtered and the solution is concentrated to a volume of 50 cubic meters.
After addition of ethyl alcoholic hydrochloric acid to a p value of 4-5, the hydrochloric acid salt of 4-dimethylaminoethyl ester of 4-n-butylamino-2oxy-benzoic acid crystallizes out and has a melting point of 156 ° C. after recrystallization from water .
This ester has a substantially lower toxicity than the dimethylaminoethyl ester of 4-butylamino-benzoic acid with approximately the same anesthetic effect. The ratio of the toxicities of the new ester to the known ester of 4-butylaminobenzoic acid in the intraperitoneal test on rats and based on cocaine = 1 is approximately 0.9: 2.5. In addition, the new ester has a bacteriostatic, in particular tuberculostatic effect .
PATENT CLAIM:
Process for the preparation of the chlorohydrate of the dimethylaminoethyl ester of 4-n butylamino-2-oxy-benzoic acid, characterized in that the dimethylamino ethyl ester of 4-amino-2-oxy-benzoic acid is used with
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE308694X | 1951-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308694A true CH308694A (en) | 1955-07-31 |
Family
ID=6121791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308694D CH308694A (en) | 1951-02-07 | 1952-01-23 | Process for the preparation of the chlorohydrate of dimethylaminoethyl ester of 4-n-butylamino-2-oxy-benzoic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308694A (en) |
-
1952
- 1952-01-23 CH CH308694D patent/CH308694A/en unknown
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